The Softail forum can best answer this, but I would think 14-17 would fit as those are the 103B motor years. Earlier models had the 96B motor, but not sure if the head pipe changed. My guess is no. The '18 and later had a motor change so no on those. I would check with your local H-D dealer first. Other places might have different brands of headers, but not too sure on the height the mufflers will get you on those.

A riding buddy has a '16 Deluxe and is looking to do the same as well. Currently he uses a big duffle bag when we take week + long trips.

 

Thanks for the information. The black bags in my pic below were and are great except they are sagging just enough to hit the mufflers. He tried to fix that but nothing seems to work.